Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H16ClF2N5O2 |
Molecular Weight | 431.823 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H](N1C=NC2=CC(Cl)=CC=C2C1=O)[C@](O)(CN3C=NC=N3)C4=CC=C(F)C=C4F
InChI
InChIKey=UHIXWHUVLCAJQL-MPBGBICISA-N
InChI=1S/C20H16ClF2N5O2/c1-12(28-11-25-18-6-13(21)2-4-15(18)19(28)29)20(30,8-27-10-24-9-26-27)16-5-3-14(22)7-17(16)23/h2-7,9-12,30H,8H2,1H3/t12-,20-/m1/s1
Molecular Formula | C20H16ClF2N5O2 |
Molecular Weight | 431.823 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20112166Curator's Comment: description was created based on several sources, including:
https://newdrugapprovals.org/2014/09/09/10613/ | http://adisinsight.springer.com/drugs/800009452
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20112166
Curator's Comment: description was created based on several sources, including:
https://newdrugapprovals.org/2014/09/09/10613/ | http://adisinsight.springer.com/drugs/800009452
Albaconazole is a triazole antifungal. Azoles are important antifungal compounds, and all drugs in this class inhibit ergosterol synthesis by blocking the 14-α-demethylase enzyme, resulting in the accumulation of toxic methylsterols that may culminate in fungal death. Albaconazole, an oral agent that has demonstrated high levels of bioavailability and potent antifungal activity. It was under development for the treatment of onychomycosis, vulvovaginal candidiasis. Also, albaconazole was evaluated in phase I, a randomized, placebo-controlled clinical trial in patients with tinea pedis. No serious adverse effects occurred in the studies involving albaconazole. However, this researches on this drug were discontinued.
Originator
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1670 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23390369 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALBACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2350 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23390369 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALBACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
226 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23390369 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-HYDROXYALBACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
235 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23390369 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-HYDROXYALBACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
107796.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23390369 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALBACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
114472.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23390369 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALBACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
51216.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23390369 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-HYDROXYALBACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
53474.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23390369 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-HYDROXYALBACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
64.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23390369 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALBACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
57.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23390369 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALBACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
67.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23390369 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-HYDROXYALBACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
72.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23390369 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-HYDROXYALBACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
Other AEs: Dizziness, Aspartate aminotransferase increased... Other AEs: Dizziness (1%) Sources: Aspartate aminotransferase increased Nause (3%) Aspartate aminotransferase increased Constipation (1%) Blood creatine phosphokinase increase (4%) vomiting (1%) Diarrhea (3%) Aspartate aminotransferase increased (2%) Upper respiratory tract infection (3%) Blood glucose increased (2%) Alanine aminotransferase increase (3%) Abdominal discomfor (1%) Gastroenteritis (1%) Neutrophil count decrease (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Aspartate aminotransferase increased | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
|
Aspartate aminotransferase increased | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
|
Abdominal discomfor | 1% | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
Constipation | 1% | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
Dizziness | 1% | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
Gastroenteritis | 1% | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
Neutrophil count decrease | 1% | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
vomiting | 1% | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
Aspartate aminotransferase increased | 2% | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
Blood glucose increased | 2% | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
Alanine aminotransferase increase | 3% | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
Diarrhea | 3% | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
Nause | 3% | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
Upper respiratory tract infection | 3% | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
Blood creatine phosphokinase increase | 4% | 400 mg 1 times / week multiple, oral (unknown) Highest studied dose Dose: 400 mg, 1 times / week Route: oral Route: multiple Dose: 400 mg, 1 times / week Sources: |
unhealthy n = 116 Health Status: unhealthy Condition: distal subungual onychomycosis Sex: M+F Food Status: UNKNOWN Population Size: 116 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones. | 1998 May 21 |
|
Specific treatment of Chagas disease: current status and new developments. | 2001 Dec |
|
In vitro antifungal activities of the new triazole UR-9825 against clinically important filamentous fungi. | 2001 Sep |
|
In vitro and in vivo efficacies of the new triazole albaconazole against Cryptococcus neoformans. | 2004 Feb |
|
In vitro interactions of licensed and novel antifungal drugs against Fusarium spp. | 2004 Jan |
|
Measurement of the sign and the magnitude of heteronuclear coupling constants from spin-state-edited J-cross-polarization NMR experiments. | 2004 Oct |
|
Emerging azole antifungals. | 2005 Feb |
|
Cryptococcus gattii: in vitro susceptibility to the new antifungal albaconazole versus fluconazole and voriconazole. | 2005 Sep |
|
Antifungal susceptibilities of the species of the Pseudallescheria boydii complex. | 2006 Dec |
|
Newer triazole antifungal agents: pharmacology, spectrum, clinical efficacy and limitations. | 2006 Jun |
|
In vitro activities of new and conventional antimycotics against fluconazole-susceptible and non-susceptible Brazilian Candida spp. isolates. | 2006 May |
|
[Identification and susceptibility against fluconazole and albaconazole of 100 yeasts' strains isolated from vaginal discharge]. | 2007 Dec 31 |
|
New and investigational triazole agents for the treatment of invasive fungal infections. | 2008 Dec |
|
Influence of Ecto-nucleoside triphosphate diphosphohydrolase activity on Trypanosoma cruzi infectivity and virulence. | 2009 |
|
Clinical safety and tolerability issues in use of triazole derivatives in management of fungal infections. | 2010 |
|
[Recent advances in the study of new antifungal lead compounds]. | 2010 Aug |
|
Design, synthesis, and structure-activity relationship studies of novel fused heterocycles-linked triazoles with good activity and water solubility. | 2014 May 8 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23706639
100, 200 and 400 mg weekly for 24 or 36 weeks.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10952601
The clinically relevant intracellular amastigote forms, proliferating in cultured Vero cells at 37°C, were more susceptible to Albaconazole than epimastigotes: the MIC required to reduce infected cells by 99% and the IC50 (concentration of the drug required to reduce infected cells by 50%) were in this case 10 nM and 1 nM, respectively.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:19:25 UTC 2023
by
admin
on
Fri Dec 15 16:19:25 UTC 2023
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Record UNII |
YDW24Y8IAB
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C514
Created by
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ALBACONAZOLE
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208952
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8195
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UU-31
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DTXSID3058244
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DB12073
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C72952
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187949-02-6
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100000124470
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SUB32139
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YDW24Y8IAB
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CHEMBL298817
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